Old Town Key West Rentals

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Our Old Town Key West rentals include both short term and monthly rentals ranging from modest studio cottages to large 5 and 6 bedroom homes. You'll find rentals in some of Old Town's most popular communities including Truman Annex, Duval Square and Windward Park. We even have pet-friendly rentals in Old Town.

Old Town Key West, on the western half of the island, is filled with rich history and contains many of our most popular attractions including the Hemingway House, Southernmost Point, Key West Lighthouse, Fort Zachary Taylor State Park, Museum of History, Mallory Square and the famous Duval Street.

Search by travel dates and filter by amenities to quickly see availability and pricing. Don't hesitate to reach out to our experienced local team with questions or for help finding and booking the perfect rental in Old Town Key West!

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Displaying 49 - 56 of 56 rentals matching your search criteria
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Old Town

Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home with a shared pool on property.

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Old Town

Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.

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Old Town

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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Old Town

Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!

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Old Town

Situated on Key West's historical Whitehead Street is Spanish Lime Cottage, appropriately named for one of the lime trees in the back yard. Whitehead runs parallel to Duval Street and is right in the heart of Old Town, Key West.

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Old Town

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Pets Not AllowedWasher/DryerPoolGated Community
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Old Town

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

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Old Town

Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle town home within easy walking distance to everything!

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